2,3-(3,6,9-Trioxaundecane-1,11-diyl-disulfan-yl)-1,4,5,8-tetra-thia-fulvalene-6,7-dicarbonitrile.

In the title compound, C(16)H(16)N(2)O(3)S(6), the two five-membered rings form a dihedral angle of 7.86 (9)°. Weak C-H⋯N hydrogen bonds link the mol-ecules to form a chain along c; the chains are further connected by weak C-H⋯O hydrogen bonds to form a three-dimensional supra-molecular network.

Related literature

For background to the use of dithiacrown ether annulated tetrathiafulvalenes as sensor molecules for various metal cations, see Moore et al. (2000 ▶); Otsubo & Ogura (1985 ▶). For the synthesis, see Yin et al. (2006 ▶). For a related structure, see Hou et al. (2009 ▶).

Experimental

Crystal data

C16H16N2O3S6

M = 476.67

Triclinic,

a = 8.300 (5) Å

b = 9.186 (5) Å

c = 13.892 (10) Å

α = 100.42 (3)°

β = 92.31 (3)°

γ = 95.60 (2)°

V = 1035.0 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.68 mm−1

T = 290 K

0.13 × 0.12 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.917, T max = 0.935

10214 measured reflections

4702 independent reflections

3936 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.088

S = 1.07

4702 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.31 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017587/ng2773sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017587/ng2773Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H16N2O3S6	Z = 2
Mr = 476.67	F(000) = 492
Triclinic, P1	Dx = 1.530 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.300 (5) Å	Cell parameters from 8487 reflections
b = 9.186 (5) Å	θ = 3.2–27.5°
c = 13.892 (10) Å	µ = 0.68 mm−1
α = 100.42 (3)°	T = 290 K
β = 92.31 (3)°	Block, black
γ = 95.60 (2)°	0.13 × 0.12 × 0.10 mm
V = 1035.0 (11) Å3

Rigaku R-AXIS RAPID diffractometer	4702 independent reflections
Radiation source: fine-focus sealed tube	3936 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.917, Tmax = 0.935	k = −10→11
10214 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.1948P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
4702 reflections	Δρmax = 0.52 e Å−3
245 parameters	Δρmin = −0.30 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (2)

Experimental. (See detailed section in the paper)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	−0.1516 (2)	0.9624 (2)	−0.20634 (12)	0.0455 (4)
C2	−0.1520 (2)	0.88171 (17)	−0.12738 (11)	0.0364 (3)
C3	−0.2869 (2)	0.84467 (18)	−0.08319 (11)	0.0377 (3)
C4	−0.4436 (2)	0.8829 (2)	−0.10925 (13)	0.0493 (4)
C5	−0.05873 (19)	0.74212 (17)	0.00468 (11)	0.0353 (3)
C6	0.02801 (19)	0.68050 (18)	0.06787 (11)	0.0374 (3)
C7	0.2533 (2)	0.60022 (18)	0.17572 (11)	0.0406 (4)
C8	0.5249 (2)	0.7500 (2)	0.28490 (13)	0.0470 (4)
H8A	0.6417	0.7629	0.2811	0.056*
H8B	0.4803	0.8258	0.2548	0.056*
C9	0.4861 (2)	0.77382 (19)	0.39115 (12)	0.0428 (4)
H9A	0.5244	0.8748	0.4233	0.051*
H9B	0.3699	0.7581	0.3967	0.051*
C10	0.5910 (3)	0.7045 (3)	0.53927 (15)	0.0621 (5)
H10A	0.6581	0.7990	0.5566	0.075*
H10B	0.6520	0.6293	0.5596	0.075*
C11	0.4441 (3)	0.7141 (2)	0.59613 (16)	0.0625 (5)
H11A	0.3571	0.6423	0.5626	0.075*
H11B	0.4667	0.6906	0.6603	0.075*
C12	0.2389 (2)	0.8716 (2)	0.64099 (13)	0.0506 (4)
H12A	0.2396	0.9632	0.6884	0.061*
H12B	0.2088	0.7892	0.6738	0.061*
C13	0.1159 (2)	0.87039 (19)	0.55895 (14)	0.0499 (4)
H13A	0.0166	0.9038	0.5853	0.060*
H13B	0.1566	0.9378	0.5171	0.060*
C14	−0.0256 (2)	0.71693 (19)	0.42162 (12)	0.0401 (4)
H14A	0.0240	0.7710	0.3747	0.048*
H14B	−0.1227	0.7616	0.4424	0.048*
C15	−0.0681 (2)	0.55669 (19)	0.37564 (12)	0.0434 (4)
H15A	−0.1587	0.5490	0.3280	0.052*
H15B	−0.1029	0.5019	0.4260	0.052*
C16	0.1146 (2)	0.56287 (17)	0.21572 (11)	0.0385 (4)
N1	−0.1521 (3)	1.0257 (2)	−0.26936 (13)	0.0688 (5)
N2	−0.5676 (2)	0.9136 (3)	−0.12990 (15)	0.0767 (6)
O1	0.56498 (15)	0.67023 (14)	0.43571 (9)	0.0494 (3)
O2	0.39558 (16)	0.85988 (14)	0.60659 (10)	0.0540 (3)
O3	0.08385 (15)	0.72386 (12)	0.50341 (8)	0.0419 (3)
S1	0.02900 (5)	0.82515 (5)	−0.08826 (3)	0.04072 (12)
S2	−0.27073 (5)	0.74152 (6)	0.00882 (3)	0.04764 (13)
S3	0.23772 (5)	0.67410 (5)	0.06743 (3)	0.04530 (12)
S4	−0.06611 (5)	0.59369 (5)	0.15614 (3)	0.04415 (12)
S5	0.44704 (6)	0.56746 (5)	0.21477 (4)	0.05140 (14)
S6	0.09787 (6)	0.47074 (5)	0.31522 (3)	0.04736 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0563 (10)	0.0477 (9)	0.0365 (8)	0.0147 (8)	0.0069 (7)	0.0124 (7)
C2	0.0451 (8)	0.0380 (8)	0.0278 (7)	0.0106 (7)	0.0008 (6)	0.0076 (6)
C3	0.0410 (8)	0.0444 (8)	0.0301 (7)	0.0123 (7)	−0.0020 (6)	0.0100 (6)
C4	0.0463 (10)	0.0674 (11)	0.0386 (9)	0.0175 (9)	0.0003 (7)	0.0160 (8)
C5	0.0369 (8)	0.0431 (8)	0.0279 (7)	0.0110 (7)	0.0006 (6)	0.0083 (6)
C6	0.0407 (8)	0.0448 (8)	0.0274 (7)	0.0113 (7)	−0.0024 (6)	0.0064 (6)
C7	0.0447 (9)	0.0432 (8)	0.0333 (8)	0.0142 (7)	−0.0099 (7)	0.0031 (6)
C8	0.0429 (9)	0.0542 (10)	0.0452 (9)	0.0016 (8)	−0.0058 (7)	0.0167 (8)
C9	0.0398 (8)	0.0426 (9)	0.0456 (9)	0.0028 (7)	−0.0038 (7)	0.0097 (7)
C10	0.0551 (11)	0.0863 (15)	0.0479 (11)	0.0191 (11)	−0.0054 (9)	0.0160 (10)
C11	0.0723 (14)	0.0645 (12)	0.0598 (12)	0.0214 (11)	0.0145 (10)	0.0259 (10)
C12	0.0559 (11)	0.0452 (9)	0.0458 (10)	0.0001 (8)	0.0052 (8)	−0.0024 (8)
C13	0.0561 (11)	0.0388 (9)	0.0544 (10)	0.0115 (8)	0.0050 (8)	0.0037 (8)
C14	0.0381 (8)	0.0480 (9)	0.0399 (8)	0.0100 (7)	0.0039 (6)	0.0202 (7)
C15	0.0413 (8)	0.0516 (9)	0.0391 (8)	−0.0083 (7)	−0.0085 (7)	0.0230 (7)
C16	0.0477 (9)	0.0382 (8)	0.0299 (7)	0.0131 (7)	−0.0096 (7)	0.0048 (6)
N1	0.0948 (14)	0.0705 (11)	0.0523 (10)	0.0233 (10)	0.0155 (9)	0.0307 (9)
N2	0.0525 (10)	0.1179 (17)	0.0673 (12)	0.0318 (11)	−0.0040 (9)	0.0268 (11)
O1	0.0477 (7)	0.0621 (8)	0.0408 (6)	0.0152 (6)	−0.0050 (5)	0.0127 (6)
O2	0.0509 (7)	0.0463 (7)	0.0644 (8)	0.0010 (6)	0.0077 (6)	0.0103 (6)
O3	0.0508 (7)	0.0355 (6)	0.0399 (6)	0.0046 (5)	−0.0055 (5)	0.0104 (5)
S1	0.0380 (2)	0.0521 (2)	0.0354 (2)	0.01113 (18)	0.00434 (16)	0.01327 (17)
S2	0.0403 (2)	0.0657 (3)	0.0470 (2)	0.0160 (2)	0.00757 (18)	0.0305 (2)
S3	0.0407 (2)	0.0629 (3)	0.0344 (2)	0.0145 (2)	−0.00208 (16)	0.01077 (19)
S4	0.0418 (2)	0.0618 (3)	0.0331 (2)	0.01220 (19)	−0.00430 (16)	0.01804 (18)
S5	0.0472 (3)	0.0551 (3)	0.0507 (3)	0.0212 (2)	−0.0144 (2)	0.0019 (2)
S6	0.0675 (3)	0.0392 (2)	0.0371 (2)	0.0133 (2)	−0.0134 (2)	0.01131 (17)

C1—N1	1.135 (2)	C10—C11	1.480 (3)
C1—C2	1.430 (2)	C10—H10A	0.9700
C2—C3	1.343 (2)	C10—H10B	0.9700
C2—S1	1.7352 (18)	C11—O2	1.420 (3)
C3—C4	1.430 (2)	C11—H11A	0.9700
C3—S2	1.7318 (18)	C11—H11B	0.9700
C4—N2	1.133 (3)	C12—O2	1.411 (2)
C5—C6	1.348 (2)	C12—C13	1.497 (3)
C5—S1	1.7615 (18)	C12—H12A	0.9700
C5—S2	1.7625 (19)	C12—H12B	0.9700
C6—S3	1.7476 (19)	C13—O3	1.420 (2)
C6—S4	1.7490 (19)	C13—H13A	0.9700
C7—C16	1.340 (3)	C13—H13B	0.9700
C7—S5	1.7479 (19)	C14—O3	1.414 (2)
C7—S3	1.764 (2)	C14—C15	1.496 (2)
C8—C9	1.505 (3)	C14—H14A	0.9700
C8—S5	1.823 (2)	C14—H14B	0.9700
C8—H8A	0.9700	C15—S6	1.814 (2)
C8—H8B	0.9700	C15—H15A	0.9700
C9—O1	1.421 (2)	C15—H15B	0.9700
C9—H9A	0.9700	C16—S6	1.7499 (19)
C9—H9B	0.9700	C16—S4	1.7555 (18)
C10—O1	1.419 (2)
N1—C1—C2	179.5 (2)	C10—C11—H11B	109.7
C3—C2—C1	123.03 (15)	H11A—C11—H11B	108.2
C3—C2—S1	118.17 (13)	O2—C12—C13	111.50 (16)
C1—C2—S1	118.78 (13)	O2—C12—H12A	109.3
C2—C3—C4	123.67 (16)	C13—C12—H12A	109.3
C2—C3—S2	118.12 (12)	O2—C12—H12B	109.3
C4—C3—S2	118.19 (14)	C13—C12—H12B	109.3
N2—C4—C3	179.9 (3)	H12A—C12—H12B	108.0
C6—C5—S1	123.07 (13)	O3—C13—C12	109.47 (15)
C6—C5—S2	121.53 (13)	O3—C13—H13A	109.8
S1—C5—S2	115.39 (9)	C12—C13—H13A	109.8
C5—C6—S3	124.32 (14)	O3—C13—H13B	109.8
C5—C6—S4	121.23 (14)	C12—C13—H13B	109.8
S3—C6—S4	114.42 (9)	H13A—C13—H13B	108.2
C16—C7—S5	125.91 (13)	O3—C14—C15	108.09 (13)
C16—C7—S3	117.11 (12)	O3—C14—H14A	110.1
S5—C7—S3	116.72 (11)	C15—C14—H14A	110.1
C9—C8—S5	114.18 (13)	O3—C14—H14B	110.1
C9—C8—H8A	108.7	C15—C14—H14B	110.1
S5—C8—H8A	108.7	H14A—C14—H14B	108.4
C9—C8—H8B	108.7	C14—C15—S6	113.74 (12)
S5—C8—H8B	108.7	C14—C15—H15A	108.8
H8A—C8—H8B	107.6	S6—C15—H15A	108.8
O1—C9—C8	107.67 (14)	C14—C15—H15B	108.8
O1—C9—H9A	110.2	S6—C15—H15B	108.8
C8—C9—H9A	110.2	H15A—C15—H15B	107.7
O1—C9—H9B	110.2	C7—C16—S6	125.35 (13)
C8—C9—H9B	110.2	C7—C16—S4	116.95 (13)
H9A—C9—H9B	108.5	S6—C16—S4	117.42 (11)
O1—C10—C11	116.36 (18)	C10—O1—C9	116.55 (15)
O1—C10—H10A	108.2	C12—O2—C11	113.79 (15)
C11—C10—H10A	108.2	C14—O3—C13	112.15 (13)
O1—C10—H10B	108.2	C2—S1—C5	94.00 (8)
C11—C10—H10B	108.2	C3—S2—C5	94.10 (8)
H10A—C10—H10B	107.4	C6—S3—C7	95.23 (8)
O2—C11—C10	109.80 (18)	C6—S4—C16	95.58 (9)
O2—C11—H11A	109.7	C7—S5—C8	101.42 (9)
C10—C11—H11A	109.7	C16—S6—C15	100.76 (8)
O2—C11—H11B	109.7

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···N1i	0.97	2.65	3.534 (3)	152
C14—H14A···N1ii	0.97	2.74	3.691 (3)	168
C14—H14B···O1iii	0.97	2.64	3.401 (3)	136
C15—H15A···O1iii	0.97	2.99	3.402 (3)	107
C9—H9A···O2iv	0.97	2.57	3.406 (3)	144
C15—H15B···O3v	0.97	2.47	3.317 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯N1i	0.97	2.65	3.534 (3)	152
C14—H14A⋯N1ii	0.97	2.74	3.691 (3)	168
C14—H14B⋯O1iii	0.97	2.64	3.401 (3)	136
C9—H9A⋯O2iv	0.97	2.57	3.406 (3)	144
C15—H15B⋯O3v	0.97	2.47	3.317 (2)	146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .